Not a game dev, so you may have tried something like this internally, and came to the conclusion it sucks/is too difficult to implement at this point etc., but why not give the option to one-click-progress events, when you have fullfilled the requirements? Like, say, in case of taking Tenten: "Take Tenten for a walk". OK. How? I ran around, tried talking to her, to othert characters (maybe they drop a hint?). Nothing. For (in-game) days, upon days nothing happened.
And then, suddenly, on one day, after I slept in my house, there was a "knock-knock" on the door, and the quest resolved itself. But now I'm left with a "???" unter Tenten, again. And again, I run around, speed up time in different locations, etc, etc., hoping for a deus ex machina moment. Again.
Or, throw in some hints, like when currently the game tell me "oh, you feel like you need to go and eat out". I do, and boom! Event. Or progress of an event.
In the same manner, for the longest time I did not know I have to use the "progress time" button, to get something (like at night, to meet Mikasa, or Amaya during the day). And you DO have many other things you may do during the day/evening.
Also things like scooby snacks/player - it was painfully frustraiting trying to get them. And then: BAM! Suddenly I (somehow, I don't even know how I got know this) got to know, that trader appears at Ichirakus.
I get it, that SOME events are special, secret, or require a set chain of events, but "normal" progress a clear "how" should be layed out.
Another example: "Preparations for the holiday". HOW do I meet Ino at the hospital? Like... how? Night time: hospital is closed. So it's only during the day. Going there does nothing, only Sakura.
Fine, so I need to get to Ino and talk to her, right? Wrong. Ino dialogue options do nothing to progress this event.
So I'm left with a bit of knowledge that tells me what starts this thing, but the game itself leaves me no obvious way of making this happen.
Also I would love to see additional reactions/dialogues after certain progression points (like when Ino's trus/lust rises, or when I get her into the lewdest outfit, with no underwear etc.).